a. Field of the Invention
This invention relates to aryloxy aminopropanols having antidepressant activity, to a process for their preparation, to intermediates used for the process, and to pharmaceutical compositions and a method of use for these aryloxy aminopropanols.
B. Prior Art
During the last few decades, psychotherapy has become more effective due to the adjunct use of new central nervous system agents, in particular, the use of tranquilizers and antidepressants. As a consequence the development of new and useful agents for psychotherapy has been diligently pursued, and the finding of a potent, well tolerated agent is noteworthy indeed.
The present invention discloses a group of antidepressant agents having these attributes. The agents are aryloxy aminopropanols. A number of aryloxy aminopropanols are known to possess pharmacologic properties; for example, 1-isopropylamino-3-(1-naphthyloxy)-2-propanol, J. W. Black, et al., Lancet, 1, 1080(1964), a potent .beta.-blocking agent, and a group of alkyl ethers of 3-amino-1-phenoxy-2-propanol derivatives, V. Dauksas and L. Pikunaite, Zh. Vses. Khim. Obshchestva im. D. I. Mendeleeva, 9, 352 (1964); Chem Abstr., 61, 6942c(1964) having a stimulating effect on the central nervous system. The compounds of the present invention are distinguished readily from the prior art compounds by having a different structural relationship with respect to the substituents. A compound, 2-isopropylamino-3-(1-naphthyloxy)-1-propanol, having the same structural relationship respecting the substituents has been reported, R. Howe, J. Med. Chem., 13 398 (1970). The compound was devoid of .beta.-receptor blocking activity in the only pharmacological testing reported therefor. When tested for anti-depressant activity according to methods described herein, the compound was found to be devoid of or to have marginal activity.